Angewandte Chemie International Edition· 2013Q1· Review
Catalytic Functionalization of C(sp<sup>2</sup>)H and C(sp<sup>3</sup>)H Bonds by Using Bidentate Directing Groups
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- 2013year
Short summary
Bidentate directing groups, such as 8-aminoquinoline and picolinamide, enable regioselective catalytic functionalization of C(sp3)-H bonds, overcoming limitations of traditional synthesis.
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Key points
- Bidentate directing groups are crucial for achieving regioselectivity in C-H bond functionalization.
- These groups facilitate the catalytic activation and transformation of C-H bonds, including challenging C(sp3)-H bonds.
- The use of directing groups bypasses the need for pre-functionalized starting materials, streamlining synthetic routes.
- Recent developments have expanded the scope of transformations possible with bidentate directing group-based systems.
AI-generated from the title and abstract; the full text is not read.
Abstract
C-H bonds are ubiquitous in organic compounds. It would, therefore, appear that direct functionalization of substrates by activation of C-H bonds would eliminate the multiple steps and limitations associated with the preparation of functionalized starting materials. Regioselectivity is an important issue because organic molecules can contain a wide variety of C-H bonds. The use of a directing group can largely overcome the issue of regiocontrol by allowing the catalyst to come into proximity with the targeted C-H bonds. A wide variety of functional groups have been evaluated for use as directing groups in the transformation of C-H bonds. In 2005, Daugulis reported the arylation of unactivated C(sp(3))-H bonds by using 8-aminoquinoline and picolinamide as bidentate directing groups, with Pd(OAc)2 as the catalyst. Encouraged by these promising results, a number of transformations of C-H bonds have since been developed by using systems based on bidentate directing groups. In this Review, recent advances in this area are discussed.
The authors' abstract, as published at the source. Angewandte Chemie International Edition, 2013 · DOI ↗
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Field: Organic Chemistry
Organic ChemistryChemistry